Aluminium lithium hydride → (6-Chloro-5-methyl-4-(methylamino)pyridin-3-yl)methanol

HRID 2404048Notes

Reaction equation

HRID 2404048 reaction equation
[Cl:1][C:2]1[C:12]([CH3:13])=[C:11]([NH:14][CH3:15])[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[C:11]([NH:14][CH3:15])[C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86713588Ethyl 6-chloro-5-methyl-4-(methylamino)nicotinate

Product 1

HCID 86713589(6-Chloro-5-methyl-4-(methylamino)pyridin-3-yl)methanolYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-chloro-5-methyl-4-(methylamino)nicotinate (2.0 g, 8.8 mmol) in tetrahydrofuran (60 mL) was added lithium aluminium hydride at 0° C., and the mixture was stirred at RT for 1.5 h. LCMS monitored the reaction was completed. The reaction was quenched by sodium sulfate decahydrate (1.5 g) and filtrated. The filtrate was concentrated to get the title compound (1.4 g, crude) as a white solid. MS (ES+) C8H11ClN2O requires: 186, 188. found: 187, 189 [M+H]+.

Workup

  1. customThe reaction was quenched by sodium sulfate decahydrate (1.5 g)
  2. filtrationfiltrated
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-769fbb0ae3eb46e18982f0685bd1de15
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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